Beating The Undertaker in a cage match in the story mode of WWF Wrestlemania 2000 for N64 was also a huge video game accomplishment for me. Between that match and facing Mankind in WWF No Mercy, I don't think I've ever been more frustrated playing a video game in my life.
When I kept losing to the 'Taker, I began blaming my cousin for my losses just because he was sitting close by. That's how frustrated I was.